(2S)-5-amino-2-{[(2S)-2-aminopropanoyl]amino}-5-oxopentanoic acid (CHEM044494)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 12:18:24 UTC
Update Date2016-11-09 01:23:08 UTC
Accession NumberCHEM044494
Identification
Common Name(2S)-5-amino-2-{[(2S)-2-aminopropanoyl]amino}-5-oxopentanoic acid
ClassSmall Molecule
DescriptionA dipeptide formed from L-alanyl and L-glutamine residues.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Alanyl-glutamineChEBI
AQChEBI
L-Ala-L-GLNChEBI
DipeptivenHMDB
N(2)-L-Alanyl-L-glutamineHMDB
Alanylglutamine, (D-glu)-isomerHMDB
(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoateHMDB
a-Q DipeptideHMDB
AQ dipeptideHMDB
Ala-GLNHMDB
Alanine glutamine dipeptideHMDB
Alanine-glutamine dipeptideHMDB
DipeptaminHMDB
GlutaMAXHMDB
Glutamax IHMDB
L-Alanyl-L-glutamineHMDB
N2-AlanylglutamineHMDB
N2-L-Alanyl-L-glutamineHMDB
SustamineHMDB
AlanylglutamineChEBI
Chemical FormulaC8H15N3O4
Average Molecular Mass217.225 g/mol
Monoisotopic Mass217.106 g/mol
CAS Registry Number39537-23-0
IUPAC Name(2S)-2-[(2S)-2-aminopropanamido]-4-carbamoylbutanoic acid
Traditional Name(2S)-2-[(2S)-2-aminopropanamido]-4-carbamoylbutanoic acid
SMILES[H][C@@](C)(N)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=O
InChI IdentifierInChI=1S/C8H15N3O4/c1-4(9)7(13)11-5(8(14)15)2-3-6(10)12/h4-5H,2-3,9H2,1H3,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1
InChI KeyHJCMDXDYPOUFDY-WHFBIAKZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty acid
  • Amino acid or derivatives
  • Amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-3.2ALOGPS
logP-4.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area135.51 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.41 m³·mol⁻¹ChemAxon
Polarizability20.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1cfb741cc8542dd66faaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000x-9000000000-28151bfc0bfe435a3d53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001l-9100000000-34b93448e98f08cd22daSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0005-4940000000-ae580540d942ca40e20fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014i-0190000000-a27c8d38b58f93ed1cceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000w-4920000000-f0232a7facacb2c78170Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001l-9800000000-5f3ab9d0267e58688a5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9100000000-02fa8594b453e49238e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udu-9600000000-6d6fb22041504ad1529fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00l2-9400000000-61e721c73725e6215defSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014l-0090000000-09b556c987a9972f84d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v4j-3970000000-66b7a75272282dd4a6c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-9610000000-7134efa0c3357e8fe160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdk-9500000000-52a78d50ccbc3b41a923Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2790000000-a6051dccaf84159ff888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xv-6910000000-d97cbce6060cc6db4e03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a000d282e0b7f61e8283Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0690000000-7883273ff04d1de6e691Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-2910000000-d67d9db5627a5074b52cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9100000000-463460ddfcf4eb7a8a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0970000000-4da7557ee9f722a95abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002n-5910000000-fc649f183ba843a20f14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-97df4c6d0ac84debe12eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11876
HMDB IDHMDB0028685
FooDB IDFDB111745
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-13403
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110464
ChEBI ID73788
PubChem Compound ID123935
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23470770
2. Bunpo P, Murray B, Cundiff J, Brizius E, Aldrich CJ, Anthony TG: Alanyl-glutamine consumption modifies the suppressive effect of L-asparaginase on lymphocyte populations in mice. J Nutr. 2008 Feb;138(2):338-43.
3. Wong SL, Doi RH: Determination of the signal peptidase cleavage site in the preprosubtilisin of Bacillus subtilis. J Biol Chem. 1986 Aug 5;261(22):10176-81.
4. Kee AJ, Smith RC, Gross AS, Madsen DC, Rowe B: The effect of dipeptide structure on dipeptide and amino acid clearance in rats. Metabolism. 1994 Nov;43(11):1373-8.
5. Holecek M, Skopec F, Sprongl L, Mraz J, Skalska H, Pecka M: Effect of alanyl-glutamine on leucine and protein metabolism in irradiated rats. Amino Acids. 2002;22(1):95-108.
6. Schiesel S, Lammerhofer M, Leitner A, Lindner W: Quantitative high-performance liquid chromatography-tandem mass spectrometry impurity profiling methods for the analysis of parenteral infusion solutions for amino acid supplementation containing L-alanyl-L-glutamine. J Chromatogr A. 2012 Oct 12;1259:111-20. doi: 10.1016/j.chroma.2012.01.020. Epub 2012 Jan 18.
7. Imamoto Y, Tanaka H, Takahashi K, Konno Y, Suzawa T: Advantages of AlaGln as an additive to cell culture medium: use with anti-CD20 chimeric antibody-producing POTELLIGENT CHO cell lines. Cytotechnology. 2013 Jan;65(1):135-43. doi: 10.1007/s10616-012-9468-8. Epub 2012 Jun 14.
8. Suojaranta-Ylinen R, Kari A, Hernesniemi J, Vapalahti M, Takala J: Hypermetabolism and increased peripheral release of amino acids after subarachnoidal hemorrhage and its operative treatment. Nutrition. 1996 May;12(5):327-33.
9. Harris RC, Hoffman JR, Allsopp A, Routledge NB: L-glutamine absorption is enhanced after ingestion of L-alanylglutamine compared with the free amino acid or wheat protein. Nutr Res. 2012 Apr;32(4):272-7. doi: 10.1016/j.nutres.2012.02.003. Epub 2012 Apr 9.